Outset - Execute JAMF Policy Once Per User

Hello,

We're being forced to move to Catalina sooner than desired and it appears that Login Hooks are finally flakey enough in JAMF for me to need another method.

What I'm trying to do is use Outset to trigger a JAMF policy once per user at login. That way, all I need to do if I want to change what it does I just modify the policy in JAMF.

The issue is that it doesn't trigger. I put it in the /usr/local/outset/login-privileged-once folder and nothing happens (I gather from the wiki that I need to put it in this folder as a policy trigger needs to run as root). I know it's not Outset that's causing the problem, as I tested a simple script that opens Safari and it works fine.

The script is as follows:

#!/bin/sh
sudo jamf policy -trigger CUSTOMEVENT
exit 0

Need to get this going by Monday, so any help would really be appreciated!

Thanks!

edit: I have Python 3.8.2 installed, along with the Command Line Tools 11.4 as those are requirements for the 3.0 version of Outset.

PS: Link to Wiki: https://github.com/chilcote/outset/wiki/Customize
Link to Outset: https://github.com/chilcote/outset